Phenylacetylene → 6-Phenylethynyl-pyridine-2-carboxylic acid

HRID 1845030Notes

Reaction equation

HRID 1845030 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:11]1([C:17]#[C:18][C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 2

HCID 10821PhenylacetyleneHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 669404046-Phenylethynyl-pyridine-2-carboxylic acidYield 93.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirring solution 0.5 g (2.4 mmol) of 6-bromo-pyridine-2-carboxylic acid, 0.05 g (0.07 mmol) of dichlorobis(triphenylphosphine)-palladium(II), and 0.015 g (0.07 mmol) of copper (I) iodide in 10 mL of NEt3, 9.9 mL of 2 N Na2CO3 solution was added 0.38 g (3.7 mmol) of phenyl acetylene under nitrogen. After 12 h reflux under nitrogen, the reaction mixture was cooled and filtered. The filtrate was acidified using 2 N HCl (pH=5), and the resulting white precipitate was filtered, washed with water and dried to afford 0.5 g (51%) of 6-phenylethynyl-pyridine-2-carboxylic acid. LCMS: 224 (M+1)+.

Workup

  1. temperatureAfter 12 h reflux under nitrogen
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. filtrationthe resulting white precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-0d0481fac47f4248a643637e2b4e3052
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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